Fuel oil stabilizer



United States Patent 3,516,806 FUEL OIL STABILIZER Robert E. Malec,Chicago, Ill., assignor, by mesne assignments, to Armour IndustrialChemical Company,

3,516,806 Patented June 23, 1970 The secondary-alkyl and cycloalkylprimary amines falling within the following formulas are operable:

Formula I a corporation of Delaware 5 Rx (CH2) CH (FH2)yR2 No Drawing.Filed Oct. 24, 1965, Ser. No. 505,000 NH:

Int. Cl. C101 1/22 wherein: US. Cl. 44-72 3 Claims R and R are selectedfrom the group consisting of hydrogen, an aryl radical, an aliphaticradical and a cycloaliphatic radical.

ABSTRACT OF THE DISCLOSURE x and y are integers having a sum from 2 to47. 132 13 igi g gfi i l gg fif 23 23 The invention accordinglycomprises the several steps amine I y y y y P y and the relation of oneor more of such steps with re- 15 spect to each of the others thereof,and a composition of matter possessing the characteristics, properties,and the relation of components, which will be exemplified in the Th1snvention relates to novel and more eifectlve fuel process andcomposition h i ft disclosed, and the 011 Stablllzefs- M0re p i yirelates to sficondary' scope of the invention will be indicated in theclaims. ifi y lf P Y amllles and use as For a fuller understanding ofthe nature and objects Stab1 11Z er$ 111 fuel of the invention,reference should be had to the follow- Distlllate fuels, such as dieseloil and furnace oil tend, ing detailed examples; with time, todeteriorate due to oxidation. Such oxidation manifests itself in theappearance of darker colors, sedi- EXAMPLE I ment, and the like.Sediment formation causes clogging 5 The indicated se ondary-alkylprimary amines are of fuel system equipment such as filters, screens,ozzles, added t0 NO. 2 fuel Oil in the concentrations indicated. burnersand other associated equipment, The resultant oil composition is thensubjected to the Th above problem i f th aggravated h standard Nalco 300F., 90-minute accelerated thermal cracked material is blended with thedistillate fuel. stablllty test- This test Consists of aging a Sample OfThe trade has devised fuel oil stabilizers to overdistillate fuel at for90 minutes, cooling to room come such problems. US. 3,084,034 and US.3,092,474 temperature, a collecting y insoluble residue y typify sucheffort. However, the optimum stabilizer must Vacuum fiitratlon through afilter p p The resultant till be found, filter paper is compared with aset of standards to ob- An object of thi inv nti i t id a novel classtain the numerical rating. Fuel color is determined after of f el oilstabilizers aging and compared with controls by the standard NPA Anotherobject is to provide a class of fuel oil stabi- 01 f m t d. lizers whichare more effective. The results are as follows:

TABLE I Rating Concentration, Filter NPA Fuel Source Additive mg./literpad color Local SBC-Cs-C7 alkyl primary amine 25 6 4 Do ..do 4 3% Dosec-01%) alkyl primary amine. 25 3 4 Do o 50 7 4 Do SeC-Cn-Cu alkylprimary amine 25 6 4 Do 50 3 3% Do 25 6 4 Do do 50 3 3% Do tert-Qz-Cnalkyl primary amine 25 7 4 Do, do. 50 s 4 D0. Control 12 5 Venezuelsec-Cn-Cn a yl y 50 2 2% Do text-C 0 alkyl primary amine 50 4 3 DoControl 4 3 1 Rating: 1=best; 20=worst.

Still another object is to provide a class of fuel oil stabilizers whichare relatively inexpensive to produce.

A further object is to provide a distillate fuel which is resistant tosedimentation and sludging.

Other objects of the invention will be part be obvious and Will in partappear hereinafter.

It has now been found that secondary-alkyl and cycloalkyl primary aminesare very effective as fuel oil stabilizers. More particularly, it hasbeen found that the secondary-alkyl and cycloalkyl primary amines suchas derived from olefins, when used in concentrations of about 10 to 150mg./liter stabilize distillate fuels, such as diesel oil, No. 2 oil,heater or furnace oil, kerosene, and the like. Also dispersal ofdeterioration products already in such fuels occurs.

EXAMPLE II The indicated secondary-alkyl primary amines are added to No.2 fuel oil including a 50-50 mixture of virgin gas oil and light cycleoil in the concentration indicated.

The resultant composition is then subjected to the proposed ASTM 16-houroxidation test. This is a test for measuring the stability of distillatefuels under accelerated oxidizing conditions. A measured volume offiltered oil is aged at a high temperature (203 F.) while oxygen isbubbled continuously through the sample. After aging and cooling, thetotal amount of insoluble matter formed is determined. More completedetails can be found in ASTM Standards (1961) Appendix XVI.

Results of this test are as follows:

TABLE II Concentration, Total gum, Fuel Source Additive mgJliter mg./100ml.

Local sec-Oq-C alkyl primary amine. 50 19. 4 Do sec- 43 alkyl primaryamine 50 12. 5 D0 Control 246. 8 50% Virgin Gas Oil, 50% Light CycleOil. Oleylamine 60 2. 1 D0 tart-C 0 alkyl primary amine 60 4. 1 Dosec-C11C15 alkyl primary amine..." 60 1. 8 D0 Control 3. 4

EXAMPLE III ylamine, sec-octadecylamine, sec-cyclohexylamine, and

all the isomeric and substituted versions thereof as Well as mixtures ofsec-alkyl and cycloalkyl primary amines and their isomeric forms such aswould be derived from various unsaturated hydrocarbons including but notlimited to the mixed C the C the C th Certain secondary-alkyl primaryamines, as indicated, are added to No. 2 fuel oil in the concentrationindicated.

The resultant composition is then subjected to the standard 16-weekstorage test at 110 F. The test is run 20 in the dark. After the 16-Weekperiod elapses, 300 ml.

samples of such aged fuel oil are filtered through tared E the 1- thethe 1 4 the 15-18 the F frit Gooch crucibles under vacuum. The gumremain- Sec'a Y and WC oalkll ammes- W W W uuu tum 10 l0 ll uilluu ltl'lull l l 14,[luluuypuuucu uluuuu WCNQIWWWWW.

l l l l l l m lll l l l w l nu We lo-u We ut we nu We it-u we 5 6 2. Adistillate fuel composition comprising distillate 2,684,292 7/1954 Caronet al. 4474 fuel and about 25 to 60 milligrams per liter of fuel of a2,758,086 8/1956 Stuart et al. 44-72 XR mixture of secondary C to Calkyl primary amines. 3,254,974 6/1966 Marsh et al. 4472 3. A distillatefuel composition comprising distillate 3,355,490 11/1967 Van Munster4472 fuel and about 25 to 60 milligrams per liter of fuel of a 5 mixtureof secondary C to C alkyl primary amines. DANIEL WYMAN Primary ExaminerY. H. SMITH, Assistant Examiner References Cited UNITED STATES PATENTSus. c1. X.R. 1,888,023 11/1932 Adams 4472 44 74; 252-401

